Tetramethyltin → HCID 67520306, compound

HRID 1925309Notes

Reaction equation

HRID 1925309 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[C:5]2I.[CH3:17][Sn](C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[C:5]2[CH3:17]

Participants

5

Reactant 2

HCID 11661TetramethyltinHCID 67520377HCID 67520377, compound

Product 1

HCID 67520306HCID 67520306, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A resealable tube was charged with methyl 6-hydroxy-4-iodo-1-naphthoate (0.302 g, 0.920 mmol), toluene (5.0 ml), tetramethyltin (0.40 g, 0.30 mL, 2.2 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.042 g, 0.036 mmol). The system was purged with argon and the tube was sealed. The mixture stirred at 90° C. for 24 h and was cooled to RT. The mixture was partitioned between EtOAc and water. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford an orange solid. This material was purified via column chromatography on silica gel (eluting with 0-50% ethyl acetate-hexane) to afford methyl 6-hydroxy-4-methyl-1-naphthoate as an orange brown solid. MS (ESI, pos. ion) m/z: 217.1 (M+H). Mass Calc'd for C13H12O3: 216.

Workup

  1. customThe system was purged with argon
  2. customthe tube was sealed
  3. temperaturewas cooled to RT
  4. customThe mixture was partitioned between EtOAc and water
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford an orange solid
  12. customThis material was purified via column chromatography on silica gel (eluting with 0-50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-655a5e4bceca463d975c19f7aaa40a3d
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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